Expanding Organoboron Chemistry:  Epoxidation of Potassium Organotrifluoroborates

Gary A. Molander* and María Ribagorda
Roy and Diana Vagelos Laboratories, Department of Chemistry. University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323
J. Am. Chem. Soc., 2003, 125 (37), pp 11148–11149
DOI: 10.1021/ja0351140
Publication Date (Web): August 19, 2003
Copyright © 2003 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, gmolandr@sas.upenn.edu

Abstract

Abstract Image

Most organoboron reagents are highly susceptible to oxidation by a variety of oxidants. In these processes, the valuable carbon−boron bond is cleaved. The organotrifluoroborates examined in this contribution appear resistant to many common oxidants. Consequently, thioether-substituted alkyltrifluoroborates can be oxidized to the corresponding sulfones, while retaining the trifluoroborate moiety. 1-Trifluoroboratoalkenes are oxidized by dioxirane, providing air-stable, crystalline oxiranyltrifluoroborates. These interesting materials are structurally analogous to oxiranyl anions, unstable intermediates that would otherwise be of tremendous synthetic utility. Finally, the first Suzuki−Miyaura coupling of an epoxytrifluoroborate has been accomplished. The chemistry described begins to expand organoboron chemistry in significant new directions.

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History

  • Published In Issue September 17, 2003
  • Received March 12, 2003

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